#884: How to Spot 10-Year Trends and Build Billion-Dollar Companies — Kevin Ryan of DoubleClick, MongoDB, Business Insider, and Many More

Kevin's Methodology Identifies Long-Term Trends Needed to Build Significant, Impactful Companies

Kevin Ryan illustrates his approach to finding enduring start-up opportunities by focusing on trends that will persist for at least ten years. He describes an exercise where he lists 20 trends he expects to last a decade on a whiteboard, considering the implications of each. This decade-long outlook is crucial because, as Kevin notes, it typically takes ten years or more to build an important company; companies built on short-lived hypes either become obsolete too quickly or become inaccessible to new entrants.

For instance, DoubleClick exemplified this philosophy: Kevin joined when it was clear that internet advertising would be a decades-long trend, not a passing fad. By expanding rapidly—entering 25 countries in the first three years compared to competitors in only six—DoubleClick established a durable moat, attracting major clients like Microsoft and Procter & Gamble. Kevin reflects that building aggressively and decisively, albeit before profitability, was essential for dominating the global market. Today, DoubleClick would be a $100 billion company if independent.

Another example is MongoDB, which rode the trend of handling unstructured data in databases—a shift that unfolded over nearly 20 years. The product's complexity meant slow initial revenue and required perseverance; for three and a half years, MongoDB had no revenue and eventually found success only by building usage over time and iteratively improving the product. Today, MongoDB is valued around $30 billion.

Kevin stresses he seeks less obvious opportunities by identifying second-order effects. A missed chance with YouTube underscores this: although he and his partners noticed falling bandwidth costs in the early 2000s, they underestimated how soon video advertising would become viable. By the time this structural cost shift made video platforms profitable, YouTube had launched and captured the market. This experience highlights Kevin's focus on tracking unit economics and cost trends, not just headline ideas, as key to spotting underappreciated opportunities.

Spotting Opportunities Requires Discerning Long-Term Trends From Temporary Excitement By Assessing if the Problem Persists and the Solution Genuinely Improves Upon Alternatives

Kevin explains that it’s essential to distinguish between lasting shifts and fleeting excitement. He employs a "business crush" test: when he has an idea that he can't stop thinking about for weeks, he pursues it, trusting his intuition more than formal business models. This ensures lasting conviction through the long, challenging process of company-building.

He also cautions that commoditized markets often force exits to avoid collapse. Kevin describes launching a platform for healthcare websites—essentially “Shopify for healthcare”—which failed because, despite an apparent enduring need, customers hesitated to adopt new solutions and the team couldn't achieve defensible scale. When it became clear there was no durable moat, they cut losses and shut down, avoiding further decline.

For a business to achieve impact, Kevin assesses scalability and whether it can build a protective moat. He references Gilt, which drove huge revenues but couldn’t secure sufficient exclusive merchandise. Even with large numbers—like being able to buy a thousand items from a vendor with 20,000 unsold units—the business lacked the scale and influence to be market-shaping. Recognizing when momentum is unsustainable is key; Kevin cites the decision to sell Gilt for $250 million when prospects dimmed, a choice that preserved value before further erosion.

Kevin's Shift From Consumer Tech to Deep Tech Acknowledges Opportunities in Structural Shifts Needing Capital and Expertise

Over time, Kevin has shifted focus away from consumer tech toward deep tech, identifying that most consumer software problems are now marginally improvable within existing e-commerce and social platforms. In contrast, structural shifts in technology—such as nuclear energy, robotics, AI infrastructure, and space—require significant capital, are shielded by high barriers ...

The Alicorp model, led by Kevin and Dwight Merriman, sets itself apart from traditional startup accelerators by taking a hands-on, focused approach to early-stage company building and prioritizing operational excellence over capital accumulation.

Alicorp's Model Differs From Typical Accelerators: Kevin and Dwight Merriman Invest $500,000 Each, Act As Co-founders, and Spend one Year On Proof of Concept Before Seeking Venture Capital

Rather than acting as a standard accelerator, where small investments are made in a range of teams with their own ideas, Kevin and Dwight Merriman each invest $500,000 into every venture, acting as active co-founders. They commit roughly a year to each company's proof-of-concept phase before seeking outside venture capital. This model requires belief in the strength of the idea and in the value that Kevin and Dwight add as partners. Their credibility, initially built on the record-setting sale of a prior New York City startup, helped attract top talent and secure capital.

Successes: Gilt, Business Insider, and Mongodb Through Kevin's Business Strategy and Dwight's Technical Management

Their approach resulted in notable success stories such as Gilt, Business Insider, and Mongodb. Kevin’s strategic guidance and Dwight’s technical management proved pivotal in these companies' early growth trajectories.

The Partnership Leveraged Kevin's Credentials From Doubleclick and Operational Expertise to Attract Executives Like Henry Blodgett Based On a Credible Vision, Ability to Raise Capital, and Conviction About the Market Opportunity

The partnership’s reputation, especially Kevin’s operational expertise and experience at Doubleclick, helped attract high-profile executives such as Henry Blodgett. Blodgett joined Business Insider after being convinced of the venture’s vision and the team’s capacity to execute and raise funds. This conviction and credibility enabled them to build teams around opportunities they deeply understood and could validate.

Building Focused Products Enables Teams to Excel, Validate Market Fit, and Expand Systematically

Kevin emphasizes the importance of focus: excelling at one thing before expanding. Starting with a niche allows the team to establish expertise and deliver superior user experiences.

Business Insider Started With Three Journalists Covering New York Tech News, Avoiding Inadequate Coverage By Expanding To Wall Street and Defense as Hiring Grew, Eventually Reaching six Hundred Journalists and one Hundred Million Monthly Unique Users

Business Insider began with only three journalists covering New York's tech beat. Their concentrated approach enabled high-quality coverage. As traffic and resources grew, they methodically expanded to other verticals such as Wall Street, defense, and retail. When sold, the company boasted about six hundred journalists and one hundred million unique monthly users, with some verticals, like defense, staffed by dedicated six-person teams.

Gilt Expanded By Starting With Weekly Women's Clothing Sales, Then Gradually Added Men's, Children's, Travel, and Home Categories, Building On Vendor Relationships and Expertise From Each Expansion

Similarly, Gilt started with just one weekly sale of women’s clothing before gradually expanding to men’s, children’s, travel, and home product lines as they built relationships and category expertise.

Discipline: Excelling At one Thing Strengthens Competitive Positioning and User Experience Over Mediocre Comprehensive Solutions

This discipline—doing one thing exceptionally well before broadening—created strong competitive positions and user loyalty, while avoiding the pitfalls of mediocrity seen in companies that try to do everything at once.

Recruiting Exceptional Talent By Focusing On Product Excellence and Growth Potential

Kevin’s hiring philosophy prioritizes CEOs and leaders with a deep understanding of product and user growth over those focused on finance or traditional marketing. The key is building a great product that drives organic user growth and network effects, not just using large budgets for advertising.

Kevin Prioritizes Ceos With Deep Product Understanding and User Growth Focus Over Financial and Marketing Strategies, as Business Insider's Growth Through Word-Of-mouth Showed the Value of Great Product Over Budgets

For example, Business Insider’s growth was achieved largely through word-of-mouth and content quality—not big marketing budgets. The strategy, considered risky by some investors, proved that investing in product and content quality can produce compounding organic growth.

Business Insider's Strategy of Not Advertising, Investing In Content Quality, and Using Social Channels and Search Seemed Reckless to Investors but Proved Superior as Content Quality Drove Network Effects and Compounding Organic Reach

Business Insider refused to advertise and instead ...

Kevin's Interest in Psychedelics Sparked by Pollan's Book and Therapeutic Potential

Kevin Ryan becomes interested in psychedelics at age 54 after reading Michael Pollan's influential book How to Change Your Mind, highlighted in the New York Times' top books of 2017. The book changes Ryan’s perspective, as he realizes that psychedelics could have significant therapeutic benefits, particularly for PTSD, depression, and anxiety. Despite the longstanding stigma from the War on Drugs, he finds that Yale’s Center for Psychedelic Research is conducting substantial academic work on these compounds, revealing misunderstood opportunities for therapeutic progress.

Ryan, who sits on Yale’s board at the time, is convinced by the research and becomes a major donor to the Yale Center for Psychedelic Research. He sees it as a genuine medical breakthrough overlooked by most of the public.

Decision to Found Transcend Therapeutics As a For-profit Company Recognized That Fda Approval for Psychedelic Medications Costs $200-$250 Million per Compound, Funding Unattainable Through Nonprofits

Ryan realizes that bringing a psychedelic compound through the FDA approval process requires $200–$250 million per drug, a barrier too high for nonprofit fundraising. In 2021, after discussions with Yale’s Professor Ben Kilmedy and Blake Mandel of Alicorp, Ryan decides the next step is founding a for-profit company to access the significant capital needed.

Together, they develop Transcend Therapeutics to focus on methylone. Methylone, as identified by Kilmedy, offers clinical advantages over MDMA, including reduced serotonin depletion, a shorter duration of action, less of a “comedown,” and the potential for weekly dosing rather than the limitations with MDMA, which can lose effect with frequent use due to increased neurotoxicity and diminished response.

Methylone's Therapeutic Properties Offer a Gentler, Shorter Experience Than Mdma, Maintaining Emotional Openness With Less Intensity, Potentially Enhancing Its Clinical Utility

Methylone is described as a “gentler, shorter-staying cousin” of MDMA. Its effects do not linger excessively, making it easier to fit within clinical treatment protocols. The emotional openness common to MDMA is preserved but with less intensity and a much shorter window of action, which Ryan and Ferriss agree could make it more clinically useful. Transcend secures a 20-year patent on using methylone for PTSD, depression, and anxiety, but due to financial constraints, chooses to initially prioritize PTSD.

Transcend's Public Benefit Incorporation Commits Shareholders to Donate 10% of Equity Gains To a Psychedelics-Focused Foundation, Ensuring Mission Alignment and Accountability Beyond Typical Corporate Structures

Transcend Therapeutics is established as a public benefit corporation. Shareholders—including Ryan, Mandel, and board members—commit to donating 10% of all equity gains to a psychedelics-focused foundation. This structure is designed to anchor the company in its social mission and prevent drift toward profit-only motives, ensuring that all stakeholders remember the commitment to improving lives through accessible PTSD treatments. Transcend plans to grant $20 million within the next nine months to causes linked to psychedelics, aiming to lead the sector in charitable giving.

Kevin's Team, With Nicolas Boileau Managing, Is Evaluating Fifty Organizations to Make Twenty Substantial Grants Instead of Five Hundred Small Ones, Aiming To Position Transcend's Foundation As the Largest Private Psychedelics Donor Next Year

Ryan’s team, with Nicolas Boileau overseeing the process, is evaluating fifty organizations with the intention of making around twenty substantial grants, rather than dispersing hundreds of smaller, less effective sums. This targeted approach seeks to position Transcend’s foundation as the largest private donor in the psychedelics field by the next year, focusing on areas and projects where they can make a significant difference.

Foundation Focuses On Neglected Areas: Group Therapy Protocols, Programs to Reduce Treatment Costs, as Individual Therapy Prices Psychedelic Treatments Beyond Reach Despite Efficacy

A primary focus of the foundation is supporting initiatives that reduce the high costs of psychedelic-assisted therapy. Ryan highlights the importance of group therapy protocols as a promising way to lower expenses, referencing the supportive dynamic seen in programs like AA. The foundation also seeks to drive innovations that lower infrastructure and delivery costs, key obstacles that restrict widespread access to potentially life-changing treatments.

Under 0.5% With Depression or Ptsd Access Promising Psychedelic Therapies, Hindered by Cost, Infr ...

Deep tech investing is gaining momentum as the limitations of consumer tech markets become increasingly clear. Investors are turning their focus to foundational industries and technologies where untapped potential and unsolved billion-dollar problems promise far greater opportunities.

Shift To Deep Tech Investing Reflects Recognition of Saturated Consumer Tech Markets Dominated by Established Platforms With Limited Room for New Entrants

Tim Ferriss describes how e-commerce has reached a ceiling in innovation: products can be delivered at lightning speed, returns are effortless, and pricing is highly competitive, leaving little room for additional improvement or new entrants. Ferriss shares that after witnessing the current state of e-commerce, he hasn't engaged with startups in that sector because key consumer problems have essentially been solved. The same logic applies to other consumer-facing tech verticals, with Kevin Ryan emphasizing that early-stage ventures are "dead" in this space due to ease of replication and dominance by existing platforms.

E-Commerce Maxed Out With Delivery, Returns, Pricing; Healthcare Costs, Energy, Robotics, Nuclear Safety Present Unsolved Multi-Billion Markets

Kevin Ryan contrasts the stagnation in consumer markets—exemplified by a proliferation of commoditized soft drinks, with 164 options competing for attention—with the vast possibilities in sectors like healthcare, energy, robotics, and nuclear safety. Unlike the crowded e-commerce field, these industries present immense problems crying out for innovation and investment. Ryan highlights the US healthcare market’s high costs and poor outcomes as one major example, justifying his firm’s focus on traditional software, AI, healthcare, and deep tech.

Commoditized Soft Drinks vs. Multi-Trillion Emerging Industries Opportunities

Ryan underscores the point with the example of soft drinks, where oversaturation means a new product is highly unlikely to break through. He contrasts this with the multi-trillion dollar opportunities emerging in areas like solar, wind, geothermal, nuclear energy, and robotics, where outstanding unsolved challenges remain and vast amounts of money will be made as new solutions take shape.

Robotics Creates Value In Controlled Environments, Not General-Purpose

Ryan predicts a massive increase in specialized robots, potentially growing by orders of magnitude in the coming years. The prime business opportunities, he states, lie in robots designed for highly specific, vertical use-cases such as those already employed in textile and car factories. These environments, which are controlled and predictable, allow robots to excel at single, well-defined tasks.

Single-Use Robots Excel In Specific Tasks Like Manufacturing, While Versatile Robots For Cooking, Cleaning, and Decision-Making Are Decades Away

Ryan emphasizes that while single-use robots that perform isolated tasks are already excelling, the dream of truly versatile robots capable of human-level multitasking—such as cooking, cleaning, or decision-making in dynamic environments—is still decades away. The flexibility and problem-solving abilities of human workers remain unmatched in roles that require varied, context-sensitive actions, like in restaurants or hospitality.

Robot Massage Therapy Tackles 17,000 Unfilled U.S. Jobs With 70% Complete Tech For Hotels, Gyms, and Spas Lacking Staff or Serving Clients Uncomfortable With Human Touch

Ryan illustrates robotics’ potential with robot massage therapy. With 17,000 unfilled massage therapy jobs across the U.S., and chronic staffing shortages in hotels, gyms, and spas, robotic massage can address concrete supply gaps and client discomfort with human touch. He estimates that the technology is already 70% of the way to being fully realized in the market.

25% Prefer Robotic to Human Massage, Showing Market Segmentation For Consistency and Reduced Discomfort

Market research reveals that 25% of people actually prefer robotic massage over human touch, either for reasons of consistency or reduced discomfort. This segmentation highlights the kind of new value that robotics—in carefully selected, high-demand niches—can unlock.

Ai's Infrastructure and Applications Offer Opportunities Beyond Consumer Chatbots, Such as Advanced Customer Service Agents That Detect Language ...

Recognizing Unsustainable Peak Intensity, Kevin Prioritized Family, Fitness, and Focused Work, Cutting Other Commitments By 80%.

Kevin Ryan develops his leadership philosophy after experiencing intense years building DoubleClick, which went public just 24 months after its founding. He realizes that maintaining an unsustainable pace would eventually lead to burnout, so he consciously prioritizes three areas: family, fitness, and focused professional work. He promotes this approach to his CEOs at DoubleClick and Alicorp, encouraging them to focus on what matters most and to trim nonessential commitments by about 80%. Ryan sacrifices time with friends, cultural events, and leisure sports, but emphasizes that these priorities prevent regret over missed family moments, especially with his children before they left for college.

4-5 Weeks of Vacation Vital for Sustainable Performance; 8-10 Weeks Possible as Alicorp Matures and Decentralizes Decision-Making

Ryan strongly advocates taking four to five weeks of vacation annually, believing it’s vital not just for performance but for creating lasting memories and connections with family. He models this behavior for his teams, understanding that leadership by example is more influential than stated policy. As Alicorp matures and its decision-making decentralizes, Ryan is able to extend his time out of the office to eight to ten weeks each year. He believes this fosters sustainable high performance and makes it feasible for others in leadership to do the same.

Kevin's Vacation Plan: Work 2-3 Hours Daily During Personal Time, Ensuring Operational Continuity; Morning Exercise—Biking, Skiing, Swimming—Followed by Focused Work For Rest and Continuity

During his time away from the office, Ryan establishes a rhythm that maintains both well-being and operational continuity. He typically works two to three hours a day, usually in the morning, to ensure the business runs smoothly. His days often begin with intensive sports such as biking, skiing, or swimming, followed by dedicated work hours scheduled to align with New York business times. Occasionally, he will adjust to a full day of work for specific needs, but overall, this structure allows him to balance rest, exercise, and leadership responsibilities without sacrificing company progress.

Kevin's Strategy for Deep Tech New York, Digital Health New York, Doc in Napa Valley, and Odyssey Adventures Focuses On Intellectual Nourishment and Talent Identification, Prioritizing Genuine Engagement Over Business Opportunity Generation

Ryan organizes and participates in various groups—Deep Tech New York, Digital Health New York, Doc in Napa Valley, and Odyssey—that are designed for intellectual growth and true engagement with emerging ideas and talent. He doesn’t approach these events primarily as business opportunity generators but as chances to nurture curiosity and facilitate genuine connections between people from diverse fields.

Groups of 30-100 From Diverse Professions Form Connections Through Structured Activities Like Hiking, Biking, and Skiing

For these events, Ryan brings together groups ranging from 30 to 100 participants from divergent professional backgrounds. The structure typically includes a morning focused on physical activity—hiking, biking, skiing—followed by sessions where attendees dive into topics like climate change, material science, nuclear energy, or consciousness. Afternoon and evening gatherings encourage deeper conversation, with structured dinners the first two nights to increase networking and the final night left open for organic socialization. His annual biking trip with eight people involves each meal centering on a 20-minute, participant-led discussion on thought-provoking subjects.

Odyssey Expedition For Venture Leaders to Investigate China's Comparative Advantages in Emerging Tech Markets

Ryan describes leading groups of venture leaders to China under the Odyssey umbrella to investigate comparative advantages in emerging tech markets. He aims to understand what China does better, facilitating dialogue among venture capitalists and other innovators.

Recruit Talent at Alicorp Events By Connecting With Industry Professionals

At all these events, Ryan focuses on connecting with industry professionals to identify and recruit new talent—sometimes for Alicorp’s needs, sometimes simply to build a rich network of capable and passionate experts. He believes in the unpredictable but positive outcomes of gathering great people together and letting interdisciplinary exchanges flourish.

Kevin Supports Immigration and Warns Against Economic Nationalism

Kevin Ryan is a strong proponent of immigration, especially for highly skilled individuals in AI and computer science. He sees bureaucratic barriers and restrictionist policies that prevent non-U.S. PhDs from joining American tech companies as self-sabotaging. Ryan argues that these talented immigrants are extremely likely to add economic value, often by joining established companies and eventually founding startups that employ thousands.

Bureaucratic Barriers Hinder Non-us Ai and Computer Science Phds From Joining American Tech Companies

Ryan criticizes current barriers that keep out talented academics and professionals, noting examples of scholars leaving the U.S. for countries like the UK and Canada due to the unwelcoming climate. He deems this a net loss for American growth and competitiveness.

Immigrants Excel In Entrepreneurship and Earnings, but Restrictionist Messaging Misrepresents Immigration As Harmful Despite Economic Benefits

He laments the political shift in recent years that frames immigrants as harmful, calling it unfathomable given that data consistently shows immigrants from diverse countries succeed in th ...